Should What You Wear Reflect Who You Are In Business?

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This week’s guest contributor is my friend, Alison Kramer, owner of Nummies and Mama to three beautiful little ones. A writer, Waldorf parent, lover of hot yoga, reluctant runner and certified twitter addict, you can read more stuff by and about Alison on her blog here and on her “What I Learned Today” posts.


We use our senses to make decisions and whether we like it or not, how something looks matters.

How we look matters. Our perception of others is rarely clear, or vise versa. Rather we see one another through a series of culturally created lenses.

Whether we build relationships online or not, we usually will eventually come face to face.  At which point there are no logos to hide behind and no airbrush that can help us.

We all start with a basic collection of features and things that make us who we are.  Gender, ethnicity, race, ability, size and others are all parts of a package we carry around with us in the world.  These shape not only our experience, but how we are perceived and experienced by others.  Of course, these are not changeable, nor should they be.  If you don’t want to do business with a short Jewish woman than that is your problem, not mine.

The question arises when we look at things we can change, like how we dress.

Like many of you reading this, I own my own business. To me, there are three major advantages to this (you will please note they are not piles of money and free time).

1. My work is my passion.  
2. I surround myself with amazing people who support, challenge and inspire.
3. I have the freedom to look and dress as I please.

For me, this means mostly Grateful Dead t-shirts, ripped jeans and no make up.  This is me, I like me and I have the benefit of being my own boss – I will not lose my position with the company or receive a memo about proper attire at work. Studies have shown that I am more intelligent and productive when I wear flip-flops.

The issue is this:

Am I doing the right thing and do I lose out on potential business for my company because of the way I look?

I have found that it is generally expected that I look a certain way, especially to those who have come to respect me online or love my brand and product before we meet. I have seen people clearly turned off when they realize the woman whose accomplishments they looked up to moments before appears to be in her 20’s (actually 34, just genetics and hot yoga)

On a business trip to New York a few weeks ago, for the first time in years, I chose to wear shoes that hurt my feet only because I wanted to look good.  They lasted about three hours (the blisters longer). When I visit retailers, go to trade shows and meet prospective clients, I do dress up a bit. I walk a line of compromise – where I can still be myself selling and marketing my product, while not needing to fight their perceptions at every turn.

I have been thinking more and more that I should just forget that and do as I please.

I may lose some customers, but I can come out the other side with a stronger brand and message.  It is a similar discussion to that of a writer or speaker who swears when they speak and/or, writes.  Should they? Can they? Why change?  I might even empower those to whom I sell, the new mom and small boutique owner, to embrace their inner Dead t-shirt and be true to themselves.

Now, I do recognize that there is a congruency possible here that might not exist if I sold insurance or was a banker, but the same time it can still hold true in many industries.  And in the end, how someone looks should not keep us from the best possible product or service.

Whether we like it or not, how we appear makes a difference in business.

Looking young, or old for that matter, being a woman or a man, how we dress, these things all change how people react to the message we are sharing…sometimes for the better, but not always.

The take home message for me is that like anything else, we have to be true to who we are, but also remember that when we put ourselves out there we cannot control how others will take us.  If like me, you are your brand and how you look is an advantage and benefit of the long hours of entrepreneurial toil – I say, rock that t-shirt and lets see who is in the market for that.

What has been your experience with perception and business?

Have you ever met any one in real life after building a relationship online and had your perceptions shattered or improved?

Should I pack my uncomfortable shoes for BlogWorld?

Would love to hear from you.


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90 responses

90 responses to “Should What You Wear Reflect Who You Are In Business?”

  1. Great, great post. Perception and influence are interesting topics close to my heart (as some of you may know). Just a name can influence how you’re treated – and your clothing? Definitely.

    In the real world, it’s very important to me that I dress in a way that I feel comfortable and able to be 150% myself.

    BUT. I do have various outfits and pieces that are for specific moments (ie, sneakers at a corporate meeting is a little much, so I have nicer shoes – that fit and don’t give me blisters – for that moment). I am never NOT myself, I am always comfortable, but I am also never shoving my identity down people’s throats, and I dress for the moment, with style and class.

    I do think that those who want to uphold the “take me as I am or leave it!” will and do lose clients; it’s a little disrespectful and egotistical not to want to meet people halfway – and also, it’s kind of dumb not to want to have enough class to make compromises.

    You don’t have to not be you, and you don’t have to stuff yourself in a suit if you love jeans, but choose the clean ones over the ripped ones, put the plain shirt instead of the Metallica one, etc etc.

    ‘Course, that’s just my POV, eh?

    • i like the “eh” makes me feel right at home 🙂 Thank you
      I think what you are speaking to, is that you have a point where you feel comfortable. Where you have found a balance between how you want to look and feel and how you feel comfortable expressing yourself to others. For everyone this would be in a different place.

    • Ha! This is funny, because as I was reading this (great!) post I was thinking of a discussion/argument I had with James about entering the “online” world and potentially leaving my 5-day-a-week suit habit in the past.

      I used a unbending rule of “always being slightly over-dressed” as a strategy, very successfully, to build up my career as a corporate consultant. In that world, having the flashy suit in the room can make the difference between winning the consulting contract …. or not.

      These days, I’ve been given the chance to adjust myself to the opposite and do the whole blogging-in-pajamas thing, which is cool. BUT, I have noticed that I have a certain set of positive “anchors” that go with being in a suit and tie… kind of like a professional/therapist state of being in the “zone” that gets switched on when the cufflinks get done up!

      I never want to lose that. So yeah… coming from the other angle… it may sound shallow, but clothes can be powerful 🙂

      • I dont think it is shallow at all. i totally agree that putting on something great and perfect for the space you’re in is a powerful tool. Just like paying attention to where we work and who we work with, what we wear is an important factor to pay attention to. To some people in some places, a suit is like a prison, to others it’s a throne
        I would miss a good suit if men didn’t wear them sometimes 🙂
        Thank you for your comment

    • I have to agree with both points of view here, but leaning a little more toward the one that says compromise. When I’m working at home and doing things around there, I tend to seriously dress down – and I’m also barefoot. However, one of the things I’ve noticed is that if I do that while I”m just out and about and simply handing out my business card, I’m not taken as seriously. (LOL Yes…I have shoes on when I’m doing that!) I think people have a certain perception of what a business owner should look like. For many, they already work for the business owner and their perceptions are shaped by that. For others, it is their management team that shapes that perception. Either way, it’s a perception that causes them to want to see someone who may not necessarily be dressed to the nines, but has at least a modicum of professionalism to their attire. I’m not saying to wear a business suit to do your errands, but even a nice top with a pair of jeans and clean sneakers (not the ones we go running in!) can go a lot further than ripped jeans with a t-shirt of Twisted Sister.

      It also depends on what you’re selling, I think. I sell jewelry, much of which can go from casual, to office, to an evening out. Even so, I try to be a little more careful about the top I put on. The slacks are comfy and the top is fashionable but nothing I’d wear on a potential date. This has worked for me because I don’t get people looking at me with surprise written all over their faces.

      I also think the perception of “business owner” is being rewritten due to the number of people venturing into that sphere due to the economy. Whereas it used to be suits and tailored shirts, now it’s gotten a little more low-key. However, it still has a bit of panache. We delineate our work self from our non-work self.

      I think one other key with the dressing may also tend to be psychological. If we dress a certain way for work and then come home and get dressed in our non-work clothes, we’re psychologically disconnecting from the work day. If you’re like me (and most other entrepreneurs) you feel like work is NEVER done – probably because it isn’t. However, I still feel it’s important to set aside a different type of clothing that delineates that full-bore work time to one that is scaled back. To that end, I think that if we make a conscious effort to look at least moderately professional – within your comfort zone! – then there is nothing wrong with that. You’re out doing what you need to and that’s key. However, scale that back to your “I’m at home” comfort zone when you’re creating or doing something less connected with customers. It gives you that psychological break while still leaving you room to step it up just a wee bit during those times you are face to face with clients or prospective clients as we never know where the next one is hiding.

      • such a great and thoughtful comment, thank you!
        i think one of the main lessons of all the comments has been the emotional affect of clothing is on our work and creativity. How empowering our clothes can be, very cool.

    • I dress working/professionals for a living. This is what I do. And I absolutely love it!

      Whether I am working with a client online, in person, or readers via my writing, I encourage people to dress in the way that they can feel connected with the “other,” but still feel authoritative and respected in what they have to say, sell, or do.

      That when they look that way, they feel that way.

      I think that is the key to the compromise approach wisely suggested.

      And we most certainly don’t ever have to feel physically uncomfortable doing it. In fact, feeling uncomfortable is an oxymoron to truly looking one’s best. I highly recommend gettin’ a better pair of shoes for BlogWorld, girl! 😉 You deserve to feel good and to look good! That way you will have more of an opportunity to forget about yourself and to fully engage in the more important endeavors at hand. The right outfit is simply another business tool. And when used wisely can bring many blessings. To limit ourselves in anyway just doesn’t make good business sense. Thanks for a great post – a topic near and dear to my heart!

  2. Oof…I really wish it didn’t, but I’ve found that what I wear directly correlates to the value my prospects perceive. Then again, I work mostly with brick and mortar businesses.

    I will say this: so far, I’ve gotten away with a well-trimmed beard and a short blonde ponytail. So maybe I wouldn’t have to play dress-up if I chose to groom differently?

    Interesting post, thanks.

    • When i was in NYC a little while ago visiting brick and mortar stores, i had a dress and shoes in my purse. There is a confession for you.
      For the first day i would change for the visits and then back, but by the second i let it go. For my retailers, baby and maternity boutiques mostly, it didn’t make a difference. At least not on this trip. It was an interesting experiment.
      Thank you for your comment 🙂

  3. Prasad says:

    Hi Jonathan, I have a different experience in this regard. In all the job interviews in which I have given and have been selected, I was wearing what I was most comfortable in (jeans, sports shoes and a casual shirt). Maybe I am fortunate to have organizations who had a liberal attitude towards clothing, but I cannot imagine myself working in a firm with uncomfortable boots 🙂

    However, agree with James POV.

    • i think “a firm with uncomfortable boots” would be a great band name… 🙂
      I agree, i think what you do and where you work is a relationship. It goes both ways and is more finding the right match more than anything.
      i know people who would be totally mortified to leave the house in jeans, but they would probably not be very happy doing what i love to do.

  4. My first bosses told me, “I didn’t hire you for what you wear, what you look like, or what hours you’re in the office – I hired you to get the job done correctly, on time, and under budget.” I stayed with him for 20 years until he closed the ad agency.

    It’s disconcerting to feel you’re under-appreciated for who you are because you are female instead of male, or are a male with a ponytail, or are wearing jeans instead of a suit, or even if you are overweight or older/younger than people’s expectations. It shouldn’t matter, but often it does…so compromise when you feel it’s best but be true to yourself always. Ultimately, your skills will shine through, it just may take longer to overcome others’ initial expectations.

    Thanks for a great post on this sensitive topic!

    • Thank you Sharon.
      i am hoping so. i am a bit of a work in progress. I must admit that it does bother me when people meet me and seem disappointed that i wasn’t “more” or “less” or “different”. But i know there is nothing that can be done about that. More about learning to trust the right people will see me,

  5. Marilia says:

    I´m sure BlogWorld will be a blast, too bad I can´t go. I haven´t met anyone from my online world in person yet, but looking forward to it.

    More than how I´m perceived, I hope I don´t get my own prejudices hold me back too much.

    • That is a great point! I do find, that i am careful to be open minded when i meet people irl for the first time. Some people do have better filters for their reactions than others.
      And as for meeting people that you know online, it changed my life in many brilliant ways. But I’m a bit of a chronic 😉
      Thank you for your comment

  6. Kristin says:

    I’ve often wondered about this too… I don’t think people consciously figure looks/clothing into a decision, but for better or worse people do seem to have unconscious biases in one direction or another.

    Probably varies a lot between industries…I am in the wedding industry, which seems very image driven.

  7. This is a wonderful post, and one that hits home with me.

    I battled exactly this issue in my first business at 23. I was traveling the US, teaching sewing classes to women 2x – 3x my age, and I found that by dressing a bit older and more classic, I sold more and gained more respect.

    It was a revelation, and led in part to writing about that topic specifically at:

    In fact, it was such a big topic, that when my students (for sewing and fashion design at the time) asked about helping them develop style, I jumped on it, because I knew just how delicate that could be, having gone through it.

    That said, I think the ideal is to find the “you” youa re confortable with, and have an array of clothing that suits even professional situations, so that you can present the image you choose AND still be comfortable.

    For example, I would say if you’re not “you” in heels, then find some amazingly cute and stylish flats for BlogHer and enjoy the heck out of it!


    • Carol B says:

      Great linked article, covers all the points I’d intended to write.

      My advise to Alison: Don’t sabotage your own hard work by creating a negative first impression with your clothes. Find a specialty store if needed to be fitted for comfortable business dress shoes – these DO exist and are about the same cost as great sneakers – and build a small interview wardrobe for your in-person meetings and conferences. For a self-employed person, every meeting is a job interview.

  8. Mike CJ says:

    I’ll look forward to seeing you at BWE – and don’t pack the uncomfortable shoes. 🙂

    Interesting post, and I have a similar dilemma as I live on a little holiday island where it’s perfectly acceptable to wear shorts, T shirt and flip flops even to meet your bank manager or accountant.

    My problem is that after ten years here, I don’t even possess what you could describe as “Business wear” or even “Smart casual” stuff.

    So look out for me at BWE – I’ll either be the guy in shorts and flip flops, or my wedding Tuxedo!

    • LOL, i like that. i do feel pretty awesome in a ball gown. Maybe i’m going in the wrong direction 😉
      also, why don’t i live on a “holiday island”?
      Thank you for your comment, and i look forward to meeting you too

  9. Rita Vail says:

    Dansko clogs are a good compromise, and they last for years. There is a shoe store on the upper upper upper west side (i72nd? or something) in NYC. It’s been 10 years since I was in the City, but they were half price and they have really good looking comfortable shoes.

    • i love this comment. i will be back in NYC in a few months and i’m going. i adore clogs

    • Allison says:

      Danskos are great. So are many of the Keens. I’m tall with big feet and old enough to feel that life is too short to wear uncomfortable shoes. I also live in a hot climate so the dreaded “panty hose” (= triple yuck factor + skin allergy) are not even a consideration.
      I agree with all the comments above about style for your own, but then have a comfort range up and down (i.e., a litte more or less on the formality scale from your starting point) so you can adjust a bit to circumstances.

      I don’t believe I AM my clothes, but that they can reflect aspects of me I want others to recognize. (However, I do believe I am my shoes. Kidding…OK, not really. ?)

  10. Carolyn says:

    It is true that others make judgements based on appearances. However, I try to dress well becauase I feel more confident in myself when I do so. I take myself more seriously and I like the way I feel. However, I am very practical when it comes to things like shoes, and I don’t buy things that are uncomfortable or don’t fit properly.

  11. Anne says:

    I started wearing what I was more and more comfortable in at the B2B business office setting I was working and over time I found I became less and less comfortable with the setting and culture…ultimately I left that job and industry. Now I am committed to be comfortable in what I wear, what I do, and where I do it…

    “To thine own self be true.”

    Living true to your personal integrity and authenticity should be your guide.

  12. Fred says:


    I 100% agree that you should always be who you are, but I don’t agree that you should where the clothes you typically where during your off hours. I think that the standard that one should use is to dress like your clients dress.

    Clothes don’t really define you, but the way you look can help build a rapport with someone you are trying to make a first impression with. And, like it or not, people typically feel most comfortable around people like themselves.

    Please don’t get me wrong, I am not suggesting that one be fake. But, instead one should try to make others feel at ease.


    • Thank you for your comment. i think wanting to make others feel comfortable is as much about your place of comfort as anything.
      i live in a world without off and on hours, where my work is my life all the time. i do find that place – where i work – is something that i do for a change in focus and attitude.
      I feel that if i am selling a product or an idea (whether that is a different thing is another post) that i need to be something people want to be like, rather than focusing on fitting in too much. But that is my place of comfort.

  13. Karen Hughes says:

    I hear you! BUT and there is a big but, you have stated when it comes to face to face meetings appearance does matter.

    It seems that it is generally accepted that 20-somethings can get away with the attitude of “I’ll wear what I want”, but when you have reached your 30’s there tends to be a shift of focus from “being all about me” to “all about the other person”.

    Although I agree that you “should” be able to dress as you please, you have to be respected by the other person first. Knowing your market and target audience goes a long way to achieving this objective but most people in their 20’s are just discovering who they really are on the inside and suspect this is in some ways the resistance to
    “dress to impress”.

    When we get over the fact that “it’s not about you” but about the way you are perceived by someone else then communication begins. Sometimes this is through dress sometimes through verbal communications and sometimes by both.

    When verbal, visual, and non-verbal all match I have found that no one really cares what you look like.

    We all want to be accepted and sometimes it starts with visual. It seems to be the easiest way to begin understanding “who” you are.

    As an Image Consultant I am passionate about helping my clients discover their true personality and emulating that on the inside and outside.

    • First of all, i love your comment.
      I am in my mid 30’s and have three children, and own and run a business i like to think of as small, successful and growing. My experience is that people who want me to look older than i do are generally people who wish they looked younger. In the end, other people’s perceptions of us are much much more about them, their values, their experiences, and their eyes, than about us.
      I prefer to have people find their place of comfort and then be the best possible people they can be. Judge for their actions, words and creations.

  14. Brew says:

    First of all, excellent post. I’m also not a big fan of dressing up for business. I do however, enjoy clothes other than t-shirts, shorts, or jeans…when the weather is right, and for the right occasion.

    I feel confident in what I do, and I feel like I want the attention to be on what I’m teaching, or how I’m performing. I don’t want you to have any sort of preconceived notion about me because of the “awesome suit” I’m wearing. I don’t want you checking to see if my socks match my shoes to compliment my pants.

    I recently posted a story similar on my blog (which I won’t link to because I feel that’s too spammy). I think it’s awesome when I find like-minded people, and I’m glad there’s other people out there that enjoy comfortable clothing and feel confident in their skills.

    Thanks again!

  15. Pat says:

    I have always considered it a fairly significant competitive advantage to dress well. Business is tough enough without putting yourself at a disadvantage by dressing poorly and sending an inadvertent message that you don’t care. My own comfort is irrelevant to my personal dress code. I dress to a professional level every day, including Fridays, because in my business you never know who your going to run into. At this point it has become a nonconformist attitude that helps differentiate my style from the masses of undifferentiated khaki’s and blue jeans.

  16. I think we play with image all through our lives. I remember packing a tie on my way to work (on my first job) and putting it on a few minutes before going into the building.

    Many years later I often find I need to put proper shoes on to work at my computer at home!

    And if I need to feel more inspired I wear my Australian hat!

    I don’t understand it either!!



  17. I love this post. Especially because I got to meet you in NY. 🙂 My take-away was how beautifully confident and relaxed you were with yourself. Did your clothes add to this overall perception? Of course. We are human and what we see is one of the first ways we try to ‘figure someone out’.
    I’ve never worked in a corporate environment. I work in sweats. But I adore clothes (costumes!) and look for opportunities to dress. I tamped this down for a long time- never wanting to make anyone feel they were underdressed- but now I’m letting that go. My choices are about me. I dress to please myself. And isn’t that what you are saying?

  18. Dahlia says:

    It is indeed inevitable to be judged by how we look. All of us are guilty of that. At a glance, products and services are judged by how it appears in front of us. The same case goes with people, how we dress matters. It matters to everyone – like it or not.
    I am not against tattered jeans and flip flops because that’s my favorite outfit. For me, dressing up should be based on comfort and how you’d like to be perceived by others. Presenting yourself well to clients is very important. If you know your clients well enough, then you know how to put up a great appearance for them and represent your own business.
    Taking care of our own business sometimes require us to be chameleons – blending. Because after all, it’s really not just about us, it’s about them too.

    • Thank you for bringing up an interesting idea. “business sometimes require us to be chameleons – blending.”
      In business we are also branding. I find that people follow and buy into things that have a strong image, or take a strong passionate stand – not or the sake of taking it – but because it is true/real/honest
      We want to noticed.
      I am not saying that for everyone it is being dressed down, that was just about me. But blending in is the last thing i want my business to do.

  19. Francoise says:

    Hi Alison

    great post, I love it – especially the fact, that you leave it open and just explain how you handle it to open up the discussion.

    We all have different ways of dressing just as we all are different and communicate in our own maner. Dressing thus is part of us and of how we communicate with others. Which is why I totaly agree with James, there is an importance to adapt to others – yet, without giving ourselves up. If your best friend has his or her wedding you’ll try to help that it is a great party – and if it means dressing up “accordingly” you’ll probably do. Just as you’ll adapt your way of communication to make “sure” to be understood.

    I thus dress as I feel comfortable and will do so a bit more in an environment where everybody knows me. If I meet people for the first time I’ll adapt in order to find a compromise which hopefully will be ok for both sides.

    In addition as said previously it is also a question of perception. Thus dressing up in a way comfortable for me might take away my chances to establish a contact. Authority and charisma are not alway perceivable at first sight – I know that I myself don’t always see all the competence others have at first sight – so why should they? 🙂

    thanks for your post!

    • I love the friend idea. you’re right, for good friends i would make those compromises. Im not sure if my best friend would ask me to feel uncomfortable for appearances. But i know many peoples friends would try.
      I also love the idea of it changing over time that you bring up, feeling more able to be as you would choose, more and more as you know someone. Because you don’t want to loose the chance to connect in the first place.
      Great comments, thank you

  20. Alison!

    I love this post, and I think I have found a kindred spirit! My home office attire is a Who t-shirt and jeans (and flip flops when I need to go out). Like you, I’m most productive when I wear what ‘feels’ good and feels most like “me.”

    When I meet with a client I toss on nicer jeans and I forego choosing from my concert t-shirt collection. Of course if the situation requires it, I bring out my business casual attire (although I still secretly feel like a rockstar ’cause of the special guitar pick I carry in my pocket). 🙂

    I must say, though, that after all these years, I still feel the internal battle of what I feel I “should” wear and what’s “appropriate.” Bottom-line: The world wants each of us to shine our lights and be all of who we are. I know which clothes make me feel most authentic and aligned with who I am, and that’s what I (generally) choose. I ‘broke the rules’ recently and wore jeans to a funeral. It was liberating. The funeral was for a high school teacher who always taught us to “be who we are.” Even though I felt funny because I was the only one dressed that way, I smiled during the service because I knew I did the right thing.

    Thanks for a fun post and some great food for thought.

    • You carry a guitar pick in your pocket! i adore you!
      I think the funeral example is very telling. Here is a time when we need one another, where our emotions are powerful, when we are celebrating a life and sharing space. That should be what it is about. i am not saying to wear your happy happy fun day shirt to a funeral, i am saying that it is not about what you are wearing. It is about you, being you, in your life with other people. And i think your teacher would have been proud of you.
      One of things i love about my kids school is the dress code. They can wear anything they want, as long as it is without a logo or movie/tv character on it. They do this so that children don’t feel badly about not having those things. because all children are beautiful and valued with our without fancy stuff.

      • My daugher’s starting school this year full time, and they have a “suggested” dress code. I’m opposed to it, because standardizing clothing means that kids won’t pick on the uniform… it’s all the same, right?

        So they’ll pick on something else. A big nose. A haircut. Body weight. Size.

        Clothes you can change. Your nose? Not so easy.

        • Very good point. it is possible i just like it because the clothes tend to be less expensive 🙂 i wore a uniform growing up, and look what happened to me!? 😉

        • James,

          I went to Catholic school from K – college and wore uniforms for 13 years of my school life.

          Believe me, kids still pick on the uniform, because even though the clothes are the same, everyone looks different in them. I was always a bit of a fashionista rebel – I’d cut the labels out of my Calvin Klein jeans and sew them on my uniform skirt hem. It made my uniform different but blended in with the plaid enough that the nuns didn’t spot it. 😉


      • Yep, I carry Pete Townshend’s guitar pick that landed at my feet during one of the shows! The object itself is a tangible representation of who I strive to be. Like Pete onstage – living out loud, giving life all ya got, not worrying about what others think. It’s a great reminder if/when I feel myself start to ‘shrink back’ in life. So when I’m dressed up at a speaking gig – not 100% comfortable in my clothes – I feel the pick in my pocket and instantly remember what I strive for. Then I get up and give a killer presentation. 🙂

        Interesting about the dress code at school – I never thought of it that way!

        Happy to have connected here. Enjoy your day!

  21. Anne Wayman says:

    I tend to slop around in my bra -less, uncombed, etc. when I’m working at home… but I do cleanup fairly well when clients are coming or I’m going out to meet them.

    A writer friend of mine swears she writes better if she’s more cleaned up than I am…

    Suspect it’s an individual thing, more or less.

  22. caitlyn says:

    Alison, I have the shoe answer for you.


    You may have to sell a few extra products to afford them, but they are GORGEOUS, look great with a Dead t-shirt, and are comfortable. They started in Vancouver and I feel a proprietary pride for no reason other than my city created such edgy loveliness (they actually are on display at the Vancouver Museum as I write.) There is a store in Toronto, and you can find them online at

  23. I’m a video producer and I have found that the idea of a Hollywood Producer is stereotyped. Its something like: guy in jeans, an ivy cap (those golf hat things that can look either really cool or really pretentious), an untucked shirt, and a sport coat. I took this cue from another producer I know and I found 2 things – its really comfortable and its almost like a costume.

    I look the part of a producer. Why? Thank Hollywood. But it also sets me in a frame of mind that fits the part. Its as much for the perceptions held by others as it is for me. I do care how people see me and I’ve decided that I am the relaxed, fun loving guy who you want to be YOUR producer because you don’t have enough fun in your life. And you get that idea first by looking at how I dress.

    • thank you so much for your comment. i would think that hollywood would be the extreme case of perception mattering, like high school times a million. I like the idea of the look being “almost like a costume” too. A tool for you to do your job as well as possible, very important point.

      • Josh Pies says:

        I look at the concept of my work dress as a costume much like I do my work environment. If I chose to work in a candle lit room with 3 monitors for computer work and a movie sound track in the background only drowned out by the sound of my pencil or the steaming of my tea pot – which is what I do often chose – then why the heck would I not also chose to dress the part of the trendy fun producer guy that I would cast in the role of trendy fun producer guy. Gee whiz, I’m always casting… but it works. My environment doesn’t start with my chair and the lighting. I’m actually just skin until I put on my closest environment – my clothes. Just a way of looking at it.

    • I read Joshua C Pies comment and smiled, firstly because of his name (how apt for a video producer to “C Pies”), secondly because what he had to say about wearing a “costume” made me stop and think about why I feel the necessity to wear one “costume” for work, a second “costume” for free time and a third for slobbing in front of my Mac late at night (i.e. my PJs) – which incidentally, is when I’m at my most creative! I started a new job at an online marketing agency a couple of months ago, after taking a 10 year career break to raise my two children. When I went for the interview I thought to myself, “Should I go with muted & professional or flamboyant interesting?” I decided on the latter, which obviously worked! However, my new colleagues are uber-relaxed in their dress code, making my “flamboyant and interesting’ style rather conspicuous. All through the summer the guys were wearing T-shirts, long shorts and flip-flops, which I found slightly unnerving (possibly because I’m about 10 years older than most of them and too much bare leg in the office can play havoc with your hormones!), so I guess that must make them more intelligent and productive than me!! In all honesty, though, I could never do the ripped jeans and heavy metal T-shirt thing, because it simply isn’t me. I’m a perfectionist and so “making do” does not exist in my repertoire! I sometimes wish I could chill out and worry less, but it’s not in my genetic make-up, nor in my creative output! I guess I’ll just have to stick with flamboyant and interesting during the day and cosy in my dressing gown at night – just to get the work done in the way that I do best :0)

  24. Q says:

    “Studies have shown that I am more intelligent and productive when I wear flip-flops.”

    Hahaha, I love that. 🙂

    • Q,

      I just clicked over to your blog from this post, read (and loved) your poems, tweeted one of ’em and then looked at your Twitter profile and realized that we live in the same damn CITY in the smallest state in the US.

      How random is THAT?

      What a small world…

  25. After being a mom entrepreneur for the past decade and working from home in my “uniform” of jeans, tees and Uggs, I can say that perception has a big impact on business and how clients and colleagues view you.

    And I can probably speak for several of us (Alison, James…) when I say that many clients and colleagues think less of us NOT when they see what we’re wearing but when they hear our children in the background.

    It’s not that we’re wearing pajamas, it’s the fact that we’re working from home while our children are present that somehow makes us seem not quite as capable or as professional anymore.

    Which really stinks because we moms do some of the most kick-ass work around the web (and the planet!) – even if we have to change a diaper in the middle of it. 😉

    Great post, Alison! Don’t pack the uncomfortable shoes – be yourself and wear what’s comfortable with pride.


    • What is it about kids and the phone? Its like a magnet.
      I have three and I understand the challenges.
      You may enjoy that this comment is being written on my blackberry from the park while they play.

      • LOL! I have three, too…and I’ve been on the phone with big buyers (One Step Ahead) or in the middle of an interview (Dave Navarro) and have had to (GASP!) change a diaper! Haha.

        If what we wear really shows who we are and what we do, then we moms should definitely be wearing capes emblazoned with our titles. Supermoms, activate!

        Nice to meet you, Alison! 😀


  26. Naomi Niles says:

    I enjoy dressing up myself. Perhaps because I spend most of my time in t-shirts and jeans. So, when I dress up, it feels fun.

    As for perceptions and what not. I’d rather over dress a little than under dress. I’m like 6′ 2″ or more in heels, so not like I’m going to be able to hide anyway, LOL.

  27. Alison,

    Thanks for a great post and a really good topic. When I practiced law in Florida, I was always conscious of how I dressed. Think about it, lawyers have to look a certain way in front of their colleagues, potential clients, juries, and judges. Then, when I had my own law firm, the concern was even more present! I was 27 years old, suing the federal government, and representing very wealthy people. There was definitely pressure in looking the part.

    I am now a coach for lawyers and I can dress in a completely different way. I work from my home office and make a conscious effort of making sure that my attire represents the artist, spiritual being, and free spirit that I am inside. For women, accessories are a really great way to do this. Even if you feel you have to wear a black suit based on the formality of the event or occasion, you can still jazz it up and show your own personality through pins, bracelets, stone rings, etc. Men can always be adventurous with their ties!

  28. Sara Chi says:

    You are very fortunate for the business you are in and you are the owner, I don’t think I’ll get any clients if I wear what you wear:) How we look Does matter, a lot. Not only should we feel comfortable in it, we should also make the people we are meeting with comfortable, and felt respected at the same time. A little politeness and manner go a long way.

    Wonder if you would change if the situations are different? Say you want your products sold in high end department stores, or worst case scenario, you need financial assistance from the bank? I do feel disappointed if someone I met online is very different than irl but until you can “trademark” yourself like Steve Jobs, we all have much to learn.

    Few more tidbits:(1)if you want to do business with Chinese people, do dress up a bit, it’s the culture:) (2)I am not a big fan of high heels either–too old for that but bloggers seem to be very receptive so no uncomfortable shoes (3) couldn’t help it but which studies have shown that you are more intelligent and productive when you wear flip-flops? Gonna post that on my site 🙂

    Thanks for this interesting and honest post.

  29. I’ve never really liked ideas like:

    -first impressions are important…
    -like it or not, people make judgements based on how you look

    I think the only reason ideas like that are “common sense” is that not enough people are willing (brave) enough to stand up and say the hell with it, I’m gonna be who I am.

    If “dressing up” (and who can say that Grateful Dead T-shirts AREN’T dressing up? 🙂 makes you feel good, then do it.

    But if you’re doing it to affect what others think… well who wants to live in a world like that?

    Rock on 🙂

  30. Pamela says:

    No need to wear uncomfortable shoes just to look polished. I wear Soffts (you can buy them at Nordstroms or Zappos) which are fashion-forward “comfort” shoes. Yes, it’s possible to be comfortable and not sacrifice style. I too do a lot of conferences, and they’ve been a godsend. I thought my days of 3 inch heels were over… but they’re back, and blister-free!

  31. The two unexpected awesome things about this post:
    1 when you all meet me, I am almost certain to look better than you were expecting
    2. All the comfy shoe suggestions. Which is awesome, because I own about 50 pairs of shoes
    🙂 poor Jonathan, I may never leave your blog, I love it so much

  32. Cori Padgett says:

    Hey Alison.. I think for me, the best way to present yourself is as yourself. However, I think that should be the best possible version of yourself.

    So if I’m comfy wearing ripped jeans and Grateful Dead t-shirts (and totally am!) then that’s what I’d wear. But maybe I’d wear them designer style.. Jeans that are meant to look ragged, not jeans so old I could have been born in them, and Grateful Dead t shirts that are fitted, not sloppy and baggy, with accents that make what I’m wearing look cool or edgy, and attention to details, such as hair, jewelry, shoes and make-up.

    Sure you can be yourself and comfortable and unique, but you can also look great doing it if you put a bit of effort in.

    Also, some folks might consider a mild compromise.. I think if you pay attention to details, you can ALWAYS reflect your true self and still look nice and pulled together for the people you meet.

    Maybe that means wearing a pair of flip flops that look dressy, paired with a dressy top and comfy jeans. Or maybe that means wearing a suit and tie, but choosing a funky tie and cuff links that reflect you, and leaving your goatee (neatly trimmed of course). Or ditching the tie altogether, and wearing your collar unbuttoned, with a nice yet stylish blazer.

    Who knows? Everyone’s tastes are different, but I firmly believe there is always a way to honor yourself and still respect other people enough not to look like a throw away when they first meet you. lol 🙂 Just my 2 cents!

    Oh and this enlightened POV has come only after years of “I don’t give a damn what you think of me, I’ll do, look, and say as I please”. lol If only I had pictures of my high school years!

    I’ve come to find there is a happy medium always, and if you’re humble and respect others as much as you respect yourself, you’ll attempt to find that place.

    • Hi Cori
      Great comment, thank you. and too bad about BWE, would have loved to meet you.
      if i told everyone how much those ripped jeans cost, they might consider me down right crazy, so i wont. 😉
      I love dressing up, just am lucky enough to be able to do it on my own terms. most days i am pretty casual, some not.

      • Cori Padgett says:

        Well of course no one need KNOW what we spend to look so great. 😉 LOL That’s like breaking girl code or something isn’t it?

        And me too, I’m a jeans and tank top kind of girl for the most part. Although there are times I like to get a little fancy, mostly I like to be comfy.

  33. Cori Padgett says:

    PS.. sooo disappointed I can’t make BlogWorld this year! ::sniffle:: Yet another person going I’d love to meet! 🙂

  34. Hey Alison, that was an ass kicking article and it hurt. Here’s why.

    One of the reason’s that Cubicle Nation goes around continuing to be mediocre is because it has no authenticity. And while marketers today love that word, you’ve either got it or you don’t. Turns out after all that you can’t bullshit your way with most people. Everybody walks around wearing the uniform because that’s what they are supposed to do. Everybody thinks a certain way or won’t jump out there and champion the new idea that will be the next breakthrough because there’s too much risk. And that’s what we are talking about here – perceived risk. If you want to be true to YOUR brand, then you either are or you aren’t – there’s no middle ground here. You can’t hedge your bets because your guests will smell it a mile away. What you wear isn’t an issue because you wear whatever you are. And here’s the totally cool thing about that – when you do that, people connect with you. And its not just people, but the people that love you and your brand and everything that you stand for. These also, incidentally, are the people that will buy what you are selling.

    I’ve struggled with this for years. I’m an explorer with an Ivy League father and mother but argyle just wasn’t ever my deal. My business suit is neoprene or down. If that’s not you, then you’re not in my tribe.

    Remember that you define yourself and your brand even more by what you’re not than by what you are. Trying to be everything to everybody is being nothing to nobody. Go into your next pin stripe board meeting wearing torn jeans and an AC/DC t-shirt. Be bold. Kick ass. Do you want to look like they think you should or do you want to give them a million dollar solution?

    • The answer to your question is that i want to be myself and spend my life learning and creating. I know enough to know that i won’t ever be able to look like everyone else wants, because that is about them, not me. I have the great pleasure of being passionate about what i do, and it is a lot of hard work, but the best part of that is being able to pave a way for myself that i am proud of. i am still learning what that will look like.
      This experience of this post has been fascinating and a pleasure. Thank you for sharing it with me 🙂

  35. Chris says:

    I think product needs to be brought into the discussion as well… you sell nursing bras, yes? You are allowed (supposed? expected?) to look like a mom — it lends you credibility. If you look like a 20-something fresh out of school, or worse, a 20-something guy, no one will take your knowledge and experience seriously. But you should look like “mom” + “business savvy entrepreneur”.

    As an artist, I’ve seen people in my field run the gamut in their dress, and the ones who do the best dress like “artist” + “intelligent” + “business savvy”. If they just dress “artsy”, people assume they’re creative but flaky. So jeans may be fine, but maybe jeans that don’t make me look like I live on food stamps 😉

  36. Elissa says:

    I’ve always subscribed to the notion that you dress for how you want to be perceived. I’m in PR, so I can ‘push the envelope’ a bit by dressing a bit more fashion forward. But PR is also by reading your audience and creating an impression that will persuade them. So, if I’m going into a formal environment, I have nothing to prove by dressing more flamboyant…I will absolutel tone it down. Sometimes I think those who shun satorial convention are simply trying too hard to be different.

    After all, it’s not personal, it’s business…most people don’t care to know who you really are…they just want to know if you can really do business.

  37. Melody says:

    Hey Allison,

    I actually read every single comment. That’s a first for me!

    Although I’ve dressed the part I was supposed to, I now dress like what is me. I’m a Jean wearing fool.

    I changed my site pics and people connect with me better if they’ve been to my site.

    I get that impressions are made on first meeting, but they will see a consistency when they meet me again in person or on my site. O say skip the fake atuff and be who you are. I believe that more people find it relaxing in the longvrun. Sure it may take longer for them to admit they judged you.

    So dress upbthe jeans however you see fit or throw on some really awesome feeling slacks, but so it because it makes you feel good, not them.

    Thanks for posting a topic that I’ve been somewhat strugglingbwith myself. You’ve helped me confirm what I should do. Stay true.

  38. […] Should What You Wear Reflect Who You Are In Business?: Brilliant concept. I, for one, am a firm believer in wearing what you want, when you want. Those […]

  39. Hi Allison!
    Great conversation here! And everyone’s points are valid. I was recently working for a company where I HAD to look the image. It was a beauty company, and I had to personify that to the customers and people I worked with. Fun at first, it increasingly wore on me, among a lot of other things with that whole atmosphere. I am currently on medical leave due to stress and anxiety from there, and I am loving scaling down and just being a comfortable shirt and blue jeans woman. I still feel naked if I don’t have on earrings, lol, but at least I have given up most other jewelry execpt for wedding rings and stud earrings. And just a little makeup when going out.
    I feel that a part of my was suffocating in that persona, that look. I do not belong there, and will not be going back at the advice of my psychiatrist. It all comes down to being true to who YOU are. I do agree that we have to meet people halfway at least, and when you are out doing business then you do have a certain image to maintain. The good thing is, when you are an entrepreneur, YOU have a lot more control over what you want that image to be!
    I plan to launch something of my own, and believe me, it will allow me to live more true to who I am!

  40. The corporate/online business world is a tough place. Whether you are preparing to start a new job at a firm or you are trying to make a bold statement through dressing, you would like to be sure that the impression you will be creating is a good one.

    Great post!

  41. Diana Maus says:

    Personally, I miss the 60s/70s. You know, different strokes for different folks and letting it all hang out? Hair? Freedom from social mores? Now we have to go back to some rule book?

    I say let your individuality groove and you will draw the kind of customers that appreciate you for who you are. Let’s not go back to the 50s. I already lived there.

  42. Diane says:

    Hi Allison,
    Thanks so much for these interesting thoughts. I have a gift box business which is based from my home office and I love the casual look and feel on a day-to-day basis, but when I go out to deliver my gifts or to meet a new business client, I always get suited up for the job, because first impressions do count. Afterall would you buy or want to purchase gifts from someone who can’t even be bothered dressing appropriately in the business world? Probably not, as you would be thinking, how can this person do a great job of sending quality presented gifts to my clients or staff? If I have business people calling on me, I always wear tidy casual during the day, when I’m at my home office, so that I don’t get caught out. This first impression with your clothes, either gets you more or the customer will take their business elsewhere.

    This same rule applies to your home office. You may only get a couple of customers, potential customers or suppliers calling on you once or twice a month, and if their first impressions are not of an organised and tidy business, will they still want to do business with you?

    I would love to change this attitude towards business dress, but unfortunately we are up against the corporate/business world with their expectations.

    I’ve apprectiated being involved in these discussions and adding my 2cents worth to the discussion. Thanks Allison for raising the subject.

  43. […] the tremendous conversation in the comments to Alison’s post about how what you wear impacts how others perceive you got me thinking. Like it or not, what we wear does seem to impact how others perceive and even […]

  44. I shared the real details in a video my biz partner Jerry and I made a while back:

    The short version is, if you opened a barbecue restaurant but called it ‘Vegan Delight’ you’d drive away your target (folks who love large hunks of meat) and confuse, annoy and offend those who came through the door because of the sign.

    I wear Hawaiian shirts, or suspenders with cargo pants. Mismatched socks, with slip-ons I can kick off when I sit down. If I wore a suit, then thought and acted the way I do, it would confuse people. Did confuse people, for years.

    Now, I wear clothing that conveys how I think and what I believe, and those who don’t want to work with me opt out pretty early in the game. Those who don’t opt out are a better match for me anyway.

    Wearing a suit because you’ll ‘get more business’ sends the message that money is more important than authenticity.

  45. Tom Bentley says:

    Alison, my ensemble features several Dead shirts (along with the Colonel Sanders on LSD one) and faded Levis are more familiar to me than my own legs. The fact that I’m a virtual worker—sometimes wondering if I’m real myself—makes it all pretty easy on the biz meeting side.

    I have found that making the slight shift to a crisp button-down shirt for the rare business meeting (and combining that with the least faded of the black jeans) makes for a considerable upgrade without much stress, and it even feels good. Since I’m a writer, my clients are grateful I don’t show up in a tube top.

  46. Elizabeth says:

    Sorry, I haven’t read all the comments but I think I have a slightly different point of view.

    I think the crux of the matter is how the clothes make YOU feel. If they make you feel totally sharp, confident, on top of your game, that is the first thing people will perceive.

    I suppose there are some extremes of outrageousness or sloppiness where this might not be true, but mainly because whatever it was (huge spiked hair, jangling piercings, smell) distracted from your presence.

    Steve Jobs comes to mind as an example. He only ever wears the black turtleneck, jeans and trainers. I would die of boredom, but it works for him because of who he is. You are not Steve Jobs, of course, but you are the you of your business. Let it shine.

  47. Phil Miller says:

    Two thoughts to add to the blender:

    1 – Everyone is treating the “what to wear at work” as an “all or nothing” one time event. I think this is a false perspective.

    I have worked as a management consultant, corporate executive and now teach at a management professor at a business school. The dress code in each situation is different and often dictated – at least at a high level, not a matter of choice. At my last corporate employer, we had a detailed list defining “business casual”., for example.

    At my university, faculty and staff have different dress codes (based in part I think on tenure vs. “fireability”).

    You still have choices within those constraints, however. I get comments on my goofy sockss and crazy watches. It’s my little expression withing the rules.

    2 – Another thought. It’s ultimately up to you. You can study how others’ non-verbal read of you matters all you want, but it comes down to what others have commented on: dress how you want.

    Just don’t go work at places that are so anti-thetical to your values (dress being one) that it’s soul killing for you and hurts your performance. If you love Greatful Dead t-shirts, better to be an entrpreneur than going to work for an F500 corporation.

    It’s all about choices.

  48. As a performing/recording artist, my eccentric (but not necessarily outlandish)look was the walk I had to & loved walking. When I became a composer I felt I had to obfuscate my identity as a Metal Industrial Creepshow barker;)
    I always got unpleasant looks from stuffy corporate types in person, but none would guess from a phone conversation or my work that I would look like someone not be welcome at a conservative potluck;) Now I don’t need to be quite as flamboyant as in the “rock star” days;)But I’ve settled in to a well dressed or casual Music Producer look that makes a lot more sense. Age and maturity have a lot to do with what kind of look you can pull off authentically.

  49. RazorX says:

    Wouldn’t it just be easier to dress nice when dealing with clients..? Then you wouldn’t have to stress-out contemplating whether they like your casual attire or not. Some clients may not care what you wear, but we do know that some do and will judge you by it. It’s just easier to dress nice and cover all the opinion bases.

  50. Thanks for the article. I guess its always a struggle to know who to please…me or them?…I think the importance is in the balance. I don’t mind going to a meeting wearing a nice suit, it can feel good from time to time, but to be honest that is so not me so its not a mask I would like to wear every single day, my performance and passion would end up affected in some kind of way.

  51. […] students read Alison Kramer’s Should What You Wear Reflect Who You Are In Business? as well as the comments on the post. In the blog entry, Kramer wonders about how she is judged as a […]